Design, Synthesis and Biochemical Evaluation of Novel Ethanoanthracenes and Related Compounds to Target Burkitt's Lymphoma

Andrew J ByrneMary J Meegan


Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt's lymphoma (BL) is a rare form of non-Hodgkin's lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2-nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17-0.38 μM against the BL cell line EBV- MUTU-1 and IC50 values in the range 0.45-0.78 μM against the chemoresistant BL cell line EBV+ DG-75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The...Continue Reading


Jan 1, 1969·Helvetica Chimica Acta·M Wilhelm, P Schmidt
Jan 27, 1998·Journal of Biochemical and Molecular Toxicology·Z XiaL Nässberger
Jul 21, 1998·International Journal of Immunopharmacology·Z XiaL Nässberger
Sep 29, 1999·Cancer Chemotherapy and Pharmacology·L G WangD R Budman
Oct 23, 2001·International Journal of Cancer. Journal International Du Cancer·J EasmonJ Hofmann
Jun 18, 2002·Immunopharmacology and Immunotoxicology·K C CarterR Waddell
Apr 2, 2003·European Journal of Medicinal Chemistry·Sandrine AlibertJacques Barbe
Jul 22, 2004·Blood·Kristie A BlumJohn C Byrd
May 5, 2005·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Elizabeth J MeredithJohn Gordon
Nov 29, 2007·Journal of Clinical Pathology·K L GroggA Dogan
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Mar 27, 2009·Bioorganic & Medicinal Chemistry Letters·Bingwei V YangJoel C Barrish
May 27, 2010·International Journal of Cancer. Journal International Du Cancer·Suzanne M Cloonan, David Clive Williams
Sep 21, 2010·Bioorganic & Medicinal Chemistry·Pei-Wen HsiehChin-Chung Wu
Jan 14, 2011·Bioorganic & Medicinal Chemistry·Yvonne M McNamaraD Clive Williams
Aug 20, 2011·Journal of Medicinal Chemistry·M Amarnath ReddyBojja Sreedhar
Jun 5, 2012·Toxicology and Applied Pharmacology·Joonghoon ParkSoon Ha Kim
Dec 18, 2013·European Journal of Medicinal Chemistry·Y M McNamaraM J Meegan
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jan 18, 2015·European Journal of Medicinal Chemistry·Alessandra BisiConcettina Cappadone
Jan 18, 2017·Adolescent Health, Medicine and Therapeutics·Massimo DozzoRenato Bassan
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Methods Mentioned

column chromatography

Software Mentioned

Bruker APEX
MOE ( Molecular Operating Environment )

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